Triethylamine → HCID 68524576, compound

HRID 1157470Notes

Reaction equation

HRID 1157470 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[C:30]([NH:34][C:35](=[O:56])[CH2:36][N:37]1[C:46](=[O:47])[C:45]2[C:40](=[CH:41][CH:42]=[C:43](I)[CH:44]=2)[N:39]=[C:38]1[C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([Cl:55])[CH:50]=1)([CH3:33])([CH3:32])[CH3:31].[CH2:57]([OH:61])[CH2:58][CH:59]=[CH2:60]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC>[C:30]([NH:34][C:35](=[O:56])[CH2:36][N:37]1[C:46](=[O:47])[C:45]2[C:40](=[CH:41][CH:42]=[C:43]([CH:60]=[CH:59][CH2:58][CH2:57][OH:61])[CH:44]=2)[N:39]=[C:38]1[C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([Cl:55])[CH:50]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 693893-Buten-1-olHCID 80271Tri-o-tolylphosphineHCID 68521671HCID 68521671, compound

Product 1

HCID 68524576HCID 68524576, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of palladium (II) acetate (82 mg, 0.37 mmol, 10 mol %) and tris (o-tolyl)phosphine (145 mg, 0.48 mmol) in anhydrous acetonitrile (40 mL) was sparged with argon for 5 minutes. Triethylamine (5.10 mL, 36.60 mmol) was added, followed by N-tert-butyl-2-[2-(3-chlorophenyl)-6-iodo-4-oxo-4H-quinazolin-3-yl]acetamide (INTERMEDIATE IV.12) (1.81 g, 3.66 mmol) and 3-buten-1-ol (1.57 mL, 18.30 mmol). The resultant mixture was heated at reflux temperature for 18 h. The resultant green suspension was concentrated in vacuo, and the residue was treated with ethyl acetate (100 mL) and filtered. The black precipitate was washed with ethyl acetate (2×50 mL), and the combined filtrates were washed with 1N HCl (aq.) (2×100 mL), brine (100 mL), dried (MgSO4) and concentrated to give the crude product as yellow-orange foam. Trituration with ether provided N-tert-butyl-2-[2-(3-chlorophenyl)-6-(4-hydroxybut-1-enyl)-4-oxo-4H-quinazolin-3-yl]acetamide (766 mg, 1.74 mmol, 48%) as an off-white powder.

Workup

  1. temperatureat reflux temperature for 18 h
  2. concentrationThe resultant green suspension was concentrated in vacuo
  3. additionthe residue was treated with ethyl acetate (100 mL)
  4. filtrationfiltered
  5. washThe black precipitate was washed with ethyl acetate (2×50 mL)
  6. washthe combined filtrates were washed with 1N HCl (aq.) (2×100 mL), brine (100 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto give the crude product as yellow-orange foam

Sources & evidence

ORD record
ord-963f8c7e68a645909d6fd98d4b7bf820
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

Loading…